Sodium hydride → 1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole

HRID 2230550Notes

Reaction equation

HRID 2230550 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].Cl[CH2:14][C:15]1[O:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:16]=1>C(OCC)(=O)C>[CH2:23]([O:22][C:20]([C:18]1[O:19][C:15]([CH2:14][N:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=[C:2]2[Cl:1])=[CH:16][CH:17]=1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 785722-ChlorobenzimidazoleHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 184649721-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Alternately, combine 2-chlorobenzimidazole (20 mmol) and sodium hydride (20 mmol) in dimethylformamidle (30 mL). After gas evolution ceases, add ethyl 5-chloromethyl-2-furoate (20 mmol) and stir. After 1 day, evaporate in vacuo to give a residue. Combine the residue and ethyl acetate. Extract with water and brine. Dry the the organic layer over Na2SO4, filter, and evaporate in vacuo to give 1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole.

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. extractionExtract with water and brine
  4. dry with materialDry the the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo

Sources & evidence

ORD record
ord-bd88fd5d7266407fa11abfbebcd6f212
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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